How to Troubleshoot Pip Proxy Setup with CNTLM?

Troubleshooting Pip Proxy Setup with CNTLM

While using CNTLM to configure pip for proxy access behind a company firewall, you may encounter errors like "Connection to proxy failed" or "Cannot fetch index." To effectively troubleshoot this issue, consider the following steps:

Verify CNTLM Setup

To check whether CNTLM is set up correctly, run the command:

cntlm.exe -c cntlm.ini -I -M http://google.com

If you receive a "Connection to proxy failed" error, review your CNTLM configuration settings and ensure that the proxy address and credentials are correct.

Use Environment Variables

Instead of using the --proxy option with pip, try setting the https_proxy environment variable to your proxy URL. Note that it should be https_proxy and not http_proxy.

export https_proxy=http://web-proxy.mydomain.com

Run Pip with Environment Variables

After setting the environment variable, run pip with the -E flag to use the modified environment settings:

sudo -E pip install somepackage

Credentials

The credentials to use are the ones you configured in the cntlm.ini file. Ensure that the username and password specified there match the credentials used by your company's proxy server.

Alternative Method

If CNTLM does not seem to resolve the issue, you can try using the following command to bypass the CNTLM proxy setup:

sudo pip -v install --proxy http://user:pass@localhost:3128 somepackage

Replace user and pass with the credentials from the cntlm.ini file.

Conclusion

By following these steps, you should be able to troubleshoot and successfully configure pip to use a proxy server with CNTLM. Remember to check your CNTLM setup, use the correct environment variable, and supply the appropriate credentials to establish a successful proxy connection for pip.

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